On a sultry evening in June, a group of impeccably dressed ladies—members of the local gentry—gathered in the loggia of Castello di Casole to reminisce about the parties they attended there decades ago. The host of those glamorous and (if the local gossip is to be believed) scandalous soirees of yore was Italian director Luchino Visconti, who occupied this 10th-century Tuscan castle in the 1960s. On this more recent occasion, however, the assembly consisted not of Marcello Mastroianni, Sophia Loren, and other cinematic luminaries but of representatives from the nearby town of Casole d’Elsa, along with guests and staff members of Timbers Resorts, which was celebrating its transformation of the 4,200-acre property near Siena into the Hotel Castello di Casole.

Within the ancient hilltop complex are now 41 suites; a 5,400-square-foot spa; the exquisitely appointed Ristorante Tosca; Pazzia Pizzeria, a more casual eatery; an expansive terrace overlooking verdant woodlands and the hotel’s immaculate infinity pool; and Bar Visconti, a clublike lounge that pays homage to the castle’s former occupant. The estate operates as a working farm, producing its own wine and olive oil, and incorporates a private game preserve. Guests who decide to take up residence (as did many of the director’s friends) may want to invest in one of the estate’s villas, available for fractional ownership, or restored farmhouses, which are available for either fractional or whole ownership.